


Hitman Dean and a 'Misunderstanding'

by plzdean



Category: Supernatural
Genre: AU, Alternate Universe, Castiel/Dean Winchester One Shot, Hand Jobs, Hitman!Dean, M/M, Misunderstandings, One Shot, Strangers, hitman dean, not so innocent castiel
Language: English
Status: Completed
Published: 2015-05-20
Updated: 2015-05-20
Packaged: 2018-03-31 11:54:47
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,214
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3977122
Author URL: https://archiveofourown.org/users/plzdean/pseuds/plzdean
Summary: <blockquote class="userstuff">
              <p>Dean Winchester is a well established hitman working for notorious drug dealer Benny Lafitte. Only this job goes a little differently than planned...</p><p>(based on a prompt).</p>
            </blockquote>





	Hitman Dean and a 'Misunderstanding'

**Author's Note:**

> pls excuse any grammatical mistakes or spelling errors etc etc, i have a migraine and my eyes hurt from staring at a computer screen too long

It was dark outside the apartment block when Dean arrived, suited up in his good old worn out combat boots and a pair of old jeans he wore to look ‘inconspicuous’, or whatever it was he was instructed to dress as. If it had not been for the sparse street lights, he wouldn’t have been able to see damned thing. The air was kinda cold too – not the kind of cold that had your teeth chatter, or the cold where your hands turned blue. It was the kind of cold where you can feel it at the tips of your fingers as the wind blows through your hair.

Dean didn’t mind, or particularly care. Soon he’d be done with this job, back home in his apartment under the hot water of his shower as the red washed down the plug hole, forgotten like all of his jobs were.

“ _Let’s get this son-of-a-bitch done with_.” He muttered, wiping away the beads of sweat that had been forming on his palms onto his jeans, feeling the gentle press of his gun tucked under his waist band where it had always stayed, ever since he was fifteen years old and his father had thrust the damned thing into his hands, telling him to ‘hold onto it’ because he’d never know when it may come in useful.

Inevitably it _had_ come in useful. Only, not in the way Dean or his father on the other hand had ever imagined. He was eighteen when it happened, down at some run down bar he happened to find himself at out of boredom. Dean, being the reckless kid he was back then spotted a small bag of powder sitting in the pocket of the guy he was sitting next to, and decided to test his luck at swiping the damned thing.

He’d barely managed to slip it into his own pocket when he found a hand clamped down on his shoulder – a hand that surely dragged him from the barstool, forced him out of the building and threw him down into a puddle in the alley way behind it.

“Gonna pay me for that?”

“Wh-”

“Don’t play dumb with me, kid. I ain’t got the time. You a cop?”

“No. No-”

“Then either pay up or this bullet is goin’ straight through that pansy skull of yours. Got it?”

Dean looked up, saw the guy was now pointing a gun at him. Dean fumbled for his own gun but he suddenly remembered he’d left it tucked up in the glove compartment of his car. “You in the army?”

“What?” The man coughed. “What the hells that gotta do with you?”

“That gun…it’s a Beretta M9.”

The man clipped the safety off and Dean froze. “Are you a damned cop, boy? Don’t lie to me this time, I don’t like liars.”

“What? No. No, I’m not. Okay? I swear. I just – you only get those guns in the army. My dad was a marine. That’s all. Did you go AWOL?”

The man’s finger hovered over the trigger. “Who’s asking?”

“Nobody. I mean, _I_ am. But I’m not a cop.” Dean picked himself up from the floor, palms up. “My dad went AWOL too. That’s how he got a gun exactly like that.”

“What’s your name, kid?” The man lowered the gun.

“Winchester. Dean Winchester. My father’s name is John. John Winchester.”

“ _Corporal_ John Winchester?”

“Yes.” Dean said quickly, slight relief lacing his breaths. “That’s him. Corporal John Winchester.”

“John Winchester is a dick.” The man said quickly, raising his gun suddenly.

Dean staggered backwards. “Don’t shoot. _Please_.”

“You with him now?”

“What?”

“John. Is he here in Austin with you?”

“No. I haven’t seen my dad in weeks, I swear. It’s just me.”

The man shot him a sceptical look and lowered the gun slowly. “John was the biggest A-hole if I ever knew one. He promised to help me get outta that shithole after I started seein’ shit that no sane person sees. Crap that wasn’t even there, you know? So he fled with me, we got the hell outta there and decided to split. Next thing I know? Sergeants show up on my doorstep to take me away to some military prison on the pretence that I deserted with a truck load of military weapons. I didn’t know shit about weapons, other than this gun. You know who has them? John Winchester has them. That bastard ratted me out.”

“Sounds like something he’d do.” Dean muttered.

“Enough of that retrospective, ‘woe is me’ crap. Gonna pay out or am I gonna have to kill you?”

“Here, take it. I don’t want it.” Dean said, holding the small plastic bag out in front of him. “I don’t want to buy it.”

“I ain’t touching shit, boy. Besides, it’s got _your_ prints on it now. If you give it back to me I’ll rat _you_ out, get you locked up in some prison. And when your piece-of-shit father comes to bail you out, I’ll be waiting in the carpark to put a bullet through _his_ head. Got it? Pay up.”

“I have no money.”

“Bullshit.”

“I don’t, okay?”

The man stopped still, thinking. “You got a gun of your own?”

“Why?”

“I’m the one asking questions here, kid. Do you have goddamn gun or not?”

“In my car.”

“Good. You’re working for me now, okay? A little payback for trying to steal my shit. Oh, and for being John Winchester’s son.”

“I am _not_ selling drugs for you.” Dean spat. “No way. I’m not going down that path.”

“Who said anything about selling drugs?” The man laughed. “No way, I wouldn’t trust a kid like you to do a job like that. That’s a suicide mission.”

“Then what?”

“You’ll be my hitman.”

“Your _what_?!”

“I ain’t saying it twice.”

“I can’t –”

“You have a gun, of course you goddamn can.” The man laughed. He then stepped closer. “And yes, actually, I will be taking that.” He swiped the small plastic bag from Dean, pulled a crumpled tissue from his pocket and placed the plastic bag inside it. “If you don’t do as I say, this is going straight to the DEA. And then I’ll be out for you and the rest of your family. Got it?”

Dean clenched his jaw, blood draining from his face. “Got it.”

“Who knows? You might even make a hobby outta it!”

 

That was five years ago. Now, twenty-three years old, Dean was still doing dirty work for a guy whom he learned was named Benny. And to be honest, he really _had_ grown to like it.

“ _Fire escape_.” Dean muttered to himself as he left the dim safety of the streetlights behind in order to venture into the pitch blackness of the ally way. Checking for accessible fire escapes was the first step to _any_ break in. “ _Any smart son-of-a-bitch knows not to leave their fire escapes easily accessible to inquisitive members of the public, such as myself_.”

Dean peered up through the darkness to find the bottom stair of the fire escape had already been let down – somebody was obviously too lazy to use to the inside stairs, or possibly too socially awkward to face the probability of bumping into talkative neighbours on the way down. Or both.

He pulled himself up onto a dumpster and stepped onto the first step of the fire escape. It creaked loudly, and Dean told himself to brace the danger and move on before a neighbour snoops on him and calls the cops. He’d been on over a hundred jobs like this, had the cops called on him thirty-seven times and counting, and still hadn’t been caught. He told himself he definitely wouldn’t let himself be caught on a job as easy as this – that would be the piss take of all piss takes.

“ _Third floor_.” Dean reminded himself as he swiftly moved up the stairs, rehearsing in his head the many possible ways to get inside the apartment. Burst through the window? Pick the lock? There was too much choice. The adrenaline was flowing.

But when Dean reached the window he paused. “ _Or was it the fifth floor?”_

He shook his head. “ _Don’t second guess yourself. Third floor_.” He reassured himself.

Gently he placed both palms and teased the window up gently. It moved freely. ‘ _Who the hell leaves a window unlocked in a neighbourhood like this_?’ he thought. It was all going smoothly, maybe even _too_ smoothly. Perhaps the poor son-of-a-bitch knew what was coming, and gave up trying to hide.

You see, the people Dean was usually sent to discard of usually had men of their own guarding the windows and doors of their homes. Dean often had to rely on sneaking into kitchens at night to lace food with arsenic, but it seemed like this job would be over and done with before he had a chance to call for back up guys to turn up with poisonous chemicals. Benny was right, this target would be a one-shot job; Dean hadn’t had one of those for a while.

Carefully he lifted the window up as far as it would go, being sure not to make a single sound, and carefully peered through a gap in the curtains in order to get a look at the room he was to be faced with. It looked pretty normal: white walls, basic floorboards, cheap Ikea furniture and a mattress on the floor. In the corner of the room was a pile of dirty laundry and a couple of empty cans of beer lay misplaced beside the bin. Various novels lay scattered amongst the sheets and Dean spotted a packet of cigarettes hidden within the sheets too. Weird. Not what he was expecting.

He peeled the curtains back and slipped into the room through the window, standing for a few minutes to listen out for any sign of somebody else actually being in the house. Sure enough, he could hear the sound of somebody brushing their teeth from one of the adjoining rooms, accompanied by the sound of running tap water.

‘ _Perhaps Benny didn’t give this guy a warning_.’ Dean thought to himself, which was weird, because Benny always gave a warning. He liked his traitors to know what was coming for them; said it gave the whole job a new air of romanticism that being a hit-man seemed to lack, which was a weird concept to believe in. But, then again Benny believed a lot of crazy shit.

Dean whipped his gun from his pocket at the sound of the door handle turning, and suddenly a dark-haired man emerged from the room, dressed in nothing but a damp purple towel around his waist.

The poor man nearly screamed when he saw Dean standing there, weapon raised.

“I…I don’t have much money buy you can take my laptop if you want? It’s…it’s kinda old and the charger is a bit temperamental but it’s the most expensive thing in this apartment.” He muttered, throwing his hands up in surrender, so fast he nearly dropped his towel.

Dean lowered the gun. “I’m not here to take your crap.”

“Wh-what are you doing here then?”

“Well, dude, I _was_ instructed to kill you, but I think I’ve got the wrong-”

The man staggered backwards, nearly tripping back into the bathroom before the door slammed shut. Dean advanced forwards, just to hear the gentle whimper from behind the door, “Just when my day couldn’t get _any_ worse. Please don’t kill me, just get the hell out. Please?”

Dean stood awkwardly in front of the door and cleared his throat. “Listen, dude, I think I must have got the wrong apartment. I’ll leave, okay, but will you let me out the front door? I don’t trust that fire escape all that much and-”

“How do I know you’re not just trying to trick me into coming out so you can kill me?”

He shrugged. He had a point. But Dean played fair. “I _promise_ I won’t kill you.”

The door opened a little and a shaking hand emerged from within out stretched. “Give me the gun so I know you won’t kill me.”

“Hell no, I’m not giving-”

“Then you’ll just have to take your chances with the fire escape.” The hand recoiled and the door shut again.

“Okay, okay, fine. Take the gun and let me out.”

The door opened a little wider this time and Dean placed the gun into the sweaty outstretched palm. Once the gun had disappeared into the bathroom, the door opened again and the dark haired man stepped out, still dressed in his towel.

“I’ll just…I’ll let you out then.” The man said slowly, awkwardly.

“Am I…going to get my gun back?” Dean asked.

The man shrugged and Dean noticed a tear roll down his cheek. A feeling of immense sympathy suddenly washed over him as he realised he was going to be the source of this poor man’s breakdown as soon as he walked out of the door; he knew he had to make up for the distress he had caused – this poor man will be traumatised for god-knows-how-long. He turned around and grabbed an old t shirt and what appeared to be a pair of joggers, and thrust them into the man’s hands. “I’m sorry about this, man. Put some clothes on, okay? What’s your name?”

“My name? No, I’m not telling you my name.  If I tell you my name you’ll probably find out all sort of personal details about me. I’ll probably turn up at work tomorrow to find you sitting at my desk with your gun, ready to try and kill me again.” The man then collapsed onto his mattress and burst into tears again. “Well, if I still _had_ a goddamn job.”

Dean sighed. “Tough day, huh?”

The man didn’t reply, just sobbed harder to the towel over his knees.

“Listen, kid, I’m not good at all this emotional crap, okay? This whole situation was a mistake. I’ll just head back out the window, okay, it’s fine. So, bye, I guess.” Dean shrugged awkwardly, making his way back across the room towards where the open window suddenly looked like the most inviting exit.

“No.”

Dean stopped suddenly.

The man's brow furrowed, eyebrows knitted together. “You can’t just _leave_.”

Dean watched as the man pulled the old t-shirt over his head, then slipping into the joggers. He stood up.

“You’re the first person I’ve had a proper conversation with in such a long time.”

“Not for nothing, dude, but I did nearly kill you. I think it’s best you let me get on with my job.”

The man ruffled his hair and looked down at the floor with a look of unmistakable sadness. Dean’s heart dropped a little. He did feel kind of bad and, plus, this guy _was_ kind of cute.

“I have some vodka in the kitchen. Or are you more of a Whiskey person? You look like a Whiskey person. I’ll go and get the Whiskey.”

Before Dean could say another word, he could already hear the sound of rummaging and the clatter of bottles from another room. A couple of seconds later, the man returned with two glasses and a bottle of cheap Whiskey. The man sat down crossed legged on the mattress and Dean didn’t quite know what to do.

“This is really nice of you, dude, but I have a job to do.” Dean said. He wanted to stay, although he wouldn’t admit that out loud. But he knew Benny would be on his back if he didn’t do what he was meant to be doing. “My boss is kinda a jerk…”

The man wasn’t listening, he was already downing the Whiskey from the bottle so fast Dean nearly dived on him before he made himself sick.

“Dude, dude, _no_. You don’t drink Whiskey like that! You’ll tear up your throat and make yourself ill. You sip it.” Dean took the bottle from the man and picked up one of the glasses from the floor. He then sat himself down beside the man and poured him an inch, handing the glass over to him. “If we’re gonna be drinking together you might as well tell me your name.”

The man took a small sip and looked up at Dean with big blue eyes he hadn’t had a chance to admire just yet. “I’m Castiel. Castiel Novak. And you?” _Novak_. That rang a bell. He brushed it off.

“I’m Dean.”

“Dean _What_?”

“Just Dean.” Dean said simply.

“Well, _Just Dean_ , is that your real name or are you trying to save your integrity for somebody else?”

“Dean _is_ my real name. But if you knew anything else about me I _would_ have to kill you.” Dean raised an eyebrow.

Castiel laughed a little. “At this point I don’t even know if you’re joking or not.”

Dean poured himself his own glass and took a mouthful, suddenly noticing the faint scent of lavender that seemed to be radiating off Castiel’s skin. It made Dean’s head spin a little. Or maybe it was the Whiskey…he couldn’t quite tell. His stomach suddenly rumbled, and Castiel looked over at him with those wide eyes again.

“You’re hungry? I can make you something to eat if you want.” Castiel climbed to his feet, but before he had a chance to run off back into the kitchen, Dean grabbed his hand and pulled him back down to the mattress again.

“I’m fine, dude, seriously. I’m not hungry.”

“You shouldn’t drink on an empty stomach.” Castiel said seriously.

“I’m not hungry.”

He noticed Castiel’s eyes dart down to where Dean was still holding Castiel’s hand maybe a little too hard.

“Crap, I’m sorry.” Dean pulled his hand away. “Was I hurting you?”

“No, you weren’t.” Castiel said quickly. “It was actually quite…”

“Weird?”

“Well, I was going to say _nice_.” Castiel said through a smile.

Nice. Dean liked the sound of that. It made him feel like he was wanted. “ _Nice_.” He repeated out loud.

He felt Castiel’s hand slip into his own again and something warm accumulated in his stomach. He’d been with a guy before, but never _romantically_. It was always just quick fucks down an alley way or a desperate hand job in a toilet cubicle; that was all he thought he ever needed, but perhaps he had been wrong.

Perhaps he really needed _this_. Sensitivity. Soft words. The scent of lavender making his breath fall short.

Dean looked back up at Castiel, but before he had a single moment to register a single ordered thought, their lips had met, moving together gently and carefully, being sure not to leave any lasting damage. Dean felt his hands move to Castiel’s cheeks, brushing a thumb over this stranger’s cheeks, tracing patterns into his skin as if he knew this new face like a map.

Castiel pushed him back gently so that Dean was now lying under him, lips still moving softly, tentatively, against each other. Dean’s hands worked down to Castiel’s waist, fingers slipping under his shirt onto his warm skin. Castiel flinched suddenly at the sudden feeling, and Dean pulled away from the kiss a little.

“You okay?”

“Your hands are cold.” Castiel mumbled into Dean’s neck.

“Oh are they?” Dean laughed, running them up and down Castiel’s back to make him squirm.

Castiel pushed away playfully and retired his head to Dean’s chest. Dean placed a hand to the back of Castiel’s head and stroked his freshly washed hair with the tips of his fingers as Castiel’s warmth radiated against him, making him feel at home for the first time in forever.

“I can hear your heart beating.” Castiel mumbled sleepily.

Dean didn’t reply, just placed a gentle kiss to the top of Castiel’s head and reached out for the pack of cigarettes lying beside his head that he’d noticed on his way in. He pulled one out of the pack and Castiel took one too, fishing for the lighter he kept in his jeans pocket. He lit Castiel’s first and then his own, discarding the lighter carelessly onto the bed beside him.

He took a long drag and breathed out a long messy breath. He looked down at Castiel to find him looking back up at him.

“I never expected my day to end like this.” Castiel muttered.

Dean took the cigarette between two fingers. “Me neither.”

Castiel sat up and stumped his cigarette out. To be honest, he really didn’t seem much like a smoker anyway. When he turned back to Dean, he took hold of his shirt and pulled it off over Dean’s head, then discarded of his own. Dean reached out to run a gentle hand across the sharp line of his collar bone, before Castiel pushed his hand away and placed his lips to Dean’s chest, littering the skin with gentle bites and kisses.

“Well to be honest,” Castiel breathed between kisses. “I don’t usually let mysterious men who break into my apartment with guns stay the night.”

“Oh, I’m staying the night now, am I?” Dean smirked.

“Obviously.” Castiel muttered into Dean’s skin.

Dean smiled and reached up to stroke the stranger’s head affectionately, when suddenly he felt a hand slip into his trousers and gently take a hold of his dick. Dean’s fingers suddenly fastened around a handful of Castiel’s hair as he let a desperate moan escape his lips. Castiel laughed.

Dean gasped, nearly dropping his cigarette. “That was…”

“Weird?”

“I was going to say nice.” Dean breathed as Castiel’s hand kept moving. He felt his crotch begin to burn hotter the faster the stranger’s hand moved. “F-uck.”

About two minutes later, Dean came quicker than he’d have liked, and the extraordinary feeling of relief and complete and utter satisfaction washed over him.

“Doesn’t take a lot to finish you off, does it?” Castiel breathed as he leant across the mattress to grab a tissue from a box on the floor.

“Usually takes longer than that.” Dean muttered awkwardly. “Something about getting a handjob off a cute stranger I nearly killed just get to me somehow.” He blew cigarette smoke out between his chapped lips and shifted his body and watched as the stranger returned to his side.

Castiel smiled. “I’ll take that as a compliment.”

Dean paused for a few moments. “Do you want me to do the same to you?”

Castiel shook his head. “Hand jobs aren’t really my thing.”

“Didn’t have a problem doing it just then.” Dean said.

“It’s different when you’re doing it to someone else.”

Dean shrugged and lay back down on the mattress.

“So…” Castiel said. “You’re a hit man, I take it. Who were you really looking for?”

Dean looked up at the ceiling, following patterns in the cracking plaster with his eyes as he spoke. “I don’t get given names. Only addresses.”

“Doesn’t sound like a precise system to me.”

Dean shrugged. “A job’s a job. In my line of work I’m not penalised for collateral.”

“And you get paid for this?”

“Yeah. Working for a drug dealer has it’s perks.”

“Who do you work for?”

Dean paused.

“Details.” Castiel remembered. “I shouldn’t have asked.”

“It’s nothing personal. You seem like a nice dude, I don’t want to get you tied up in all this shit.” Dean took a drag from his cigarette.

Castiel placed his head gently on Dean’s chest again and let out a long happy sigh. He yawned. Dean’s heart fluttered. He really _was_ cute, and Dean hated himself for the way he fell so quickly for people.

Perhaps this was the beginning of a _real_ relationship, the kind he’d always imagined himself having. The kind where you wake up to the sound of the other’s snores and feel content, or the kind where you take it in turns to cook that evening’s meals. He’d always dreamed of having someone to come home to, someone to look after him and make him feel secure for once.

But when your life revolves around a notorious criminal, it’s too dangerous to have people that close; people like Benny Lafitte don’t care if it takes a bullet to the head of a sweet guy you met at a bar the night before in order to get you out of bed and onto your next job. Dean had learnt that the hard way.

Perhaps Castiel was worth the risk?

“Sleepy?”

Castiel nodded. “I am.”

Dean reached up to stroke his hair again and the scent of lavender began to make him drowsy. The next thing he knew, Castiel was snoring peacefully on top of him, and he had no choice but to close his eyes and let sleep take him too.

***

 When Dean awoke the next morning he found himself alone. But as he stretched and sat up slowly, he found Castiel sitting in a chair across the room with his gun in hand.

“Good morning, Dean.” Castiel said smiled, spinning the gun effortlessly around his index finger.

“What the- is that my gun?!”

Castiel unclipped the safety and held the gun out. “Dean Winchester, Does Benny Laffite know his hitmen are as easy to charm as you are?”

**Author's Note:**

> kudos if u liked it :)) <3


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